Potassium Carbonate → 4-{4-[3-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]-1-piperidinyl}butanoic acid

HRID 1942764Notes

Reaction equation

HRID 1942764 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][N:15]=[C:14]([C:17]3[C:18]([CH2:29][CH3:30])=[C:19]([CH:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[CH:20]=[CH:21][CH:22]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].Br[CH2:32][CH2:33][CH2:34][C:35]([O:37]CC)=[O:36].C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>CN(C)C=O.CC(O)=O.O.C(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][N:15]=[C:14]([C:17]3[C:18]([CH2:29][CH3:30])=[C:19]([CH:23]4[CH2:28][CH2:27][N:26]([CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36])[CH2:25][CH2:24]4)[CH:20]=[CH:21][CH:22]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 76300Ethyl 4-bromobutyrateHCID 58494034HCID 58494034, compound

Product 1

HCID 545795974-{4-[3-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]-1-piperidinyl}butanoic acidYield 48.1%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]piperidine (D122) (108 mg, 0.244 mmol) and ethyl 4-bromobutanoate (95 mg, 0.489 mmol) in N,N-Dimethylformamide (DMF) (8 mL) was added K2CO3 (223 mg, 1.614 mmol). This solution was sealed and stirred for overnight at room temperature. To the above solution was added Isopropanol (10.00 mL) and Water (2 mL) and sodium hydroxide (0.5 mL, 3.05 mmol). The solution was sealed and stirred for 5 h at 40° C. The reaction was neutrolized by AcOH, dried and purified by Mass Directed AutoPrep to afford 4-{4-[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]-1-piperidinyl}butanoic acid (E102) (62 mg) as a TFA salt.

Workup

  1. customThis solution was sealed
  2. customThe solution was sealed
  3. stirringstirred for 5 h at 40° C
  4. customdried
  5. custompurified by Mass Directed AutoPrep

Sources & evidence

ORD record
ord-fb6df607ebc447998544fdf1d3f6ee09
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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